2-Methyl-6-(trifluoro-meth-yl)imidazo[1,2-a]pyridine-3-carbonitrile.

In the title compound, C(10)H(6)F(3)N(3), the imidazo[1,2-a]pyridine group is essentially planar with a maximum deviation of 0.021 (1) Å. The F atoms in the trifluoro-methyl group and the methyl H atoms are each disordered over two sets of sites with refined site occupancies of 0.68 (1):0.32 (1). In the crystal, mol-ecules are linked into infinite chains through two C-H⋯N inter-actions forming R(2) (2)(12) and R(2) (2)(8) hydrogen-bond ring motifs. These chains are stacked along the a axis.

Related literature

For the biological activity of imidazole derivatives, see: Biftu et al. (2006 ▶); Elhakmoui et al. (1994 ▶); Fisher & Lusi (1972 ▶); Gudmundsson & Johns (2003 ▶, 2007 ▶); Kaminski et al. (1989 ▶); Rewankar et al. (1975 ▶); Rupert et al. (2003 ▶). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H6F3N3

M = 225.18

Monoclinic,

a = 5.6871 (3) Å

b = 8.5437 (5) Å

c = 20.5403 (13) Å

β = 96.653 (4)°

V = 991.31 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 297 K

0.43 × 0.22 × 0.07 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.945, T max = 0.991

10175 measured reflections

2820 independent reflections

1720 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.130

S = 1.03

2820 reflections

176 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003928/fl2329sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003928/fl2329Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H6F3N3	F(000) = 456
Mr = 225.18	Dx = 1.509 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2837 reflections
a = 5.6871 (3) Å	θ = 2.6–25.3°
b = 8.5437 (5) Å	µ = 0.13 mm−1
c = 20.5403 (13) Å	T = 297 K
β = 96.653 (4)°	Plate, colourless
V = 991.31 (10) Å3	0.43 × 0.22 × 0.07 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	2820 independent reflections
Radiation source: fine-focus sealed tube	1720 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 29.8°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.945, Tmax = 0.991	k = −11→11
10175 measured reflections	l = −28→28

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.0655P] where P = (Fo2 + 2Fc2)/3
2820 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R– factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C10	0.2247 (4)	0.2282 (2)	0.30231 (9)	0.0633 (5)
F1	0.1174 (15)	0.0950 (4)	0.2794 (3)	0.1138 (18)	0.675 (13)
F2	0.3304 (7)	0.2905 (11)	0.2575 (3)	0.134 (2)	0.675 (13)
F3	0.0427 (9)	0.3205 (5)	0.3079 (2)	0.0858 (13)	0.675 (13)
F1A	0.246 (3)	0.1157 (11)	0.2609 (4)	0.097 (3)	0.325 (13)
F2A	0.329 (2)	0.3390 (12)	0.2678 (6)	0.131 (4)	0.325 (13)
F3A	0.0178 (17)	0.271 (2)	0.3077 (6)	0.141 (5)	0.325 (13)
N1	0.46963 (19)	0.24647 (12)	0.47742 (6)	0.0410 (3)
N2	0.7873 (2)	0.15187 (14)	0.54049 (6)	0.0528 (3)
N3	0.1553 (2)	0.49667 (17)	0.57317 (7)	0.0660 (4)
C1	0.3230 (3)	0.27046 (16)	0.42094 (8)	0.0447 (4)
H1A	0.1888	0.3328	0.4206	0.054*
C2	0.3776 (3)	0.20129 (17)	0.36531 (7)	0.0478 (4)
C3	0.5809 (3)	0.10468 (18)	0.36599 (8)	0.0541 (4)
H3A	0.6161	0.0581	0.3274	0.065*
C4	0.7237 (3)	0.07997 (17)	0.42235 (8)	0.0530 (4)
H4A	0.8554	0.0153	0.4228	0.064*
C5	0.6712 (2)	0.15294 (16)	0.48021 (8)	0.0455 (4)
C6	0.6634 (3)	0.24616 (17)	0.57735 (8)	0.0486 (4)
C7	0.4662 (2)	0.30593 (16)	0.54019 (7)	0.0432 (3)
C8	0.2918 (3)	0.40991 (17)	0.55779 (7)	0.0468 (4)
C9	0.7402 (3)	0.2770 (2)	0.64782 (8)	0.0654 (5)
H9A	0.7533	0.1797	0.6713	0.098*	0.675 (13)
H9B	0.6256	0.3425	0.6654	0.098*	0.675 (13)
H9C	0.8910	0.3287	0.6523	0.098*	0.675 (13)
H9D	0.8904	0.2278	0.6603	0.098*	0.325 (13)
H9E	0.6250	0.2353	0.6738	0.098*	0.325 (13)
H9F	0.7547	0.3878	0.6549	0.098*	0.325 (13)

	U11	U22	U33	U12	U13	U23
C10	0.0701 (12)	0.0666 (11)	0.0522 (10)	0.0091 (10)	0.0024 (9)	−0.0014 (8)
F1	0.131 (3)	0.0749 (15)	0.117 (3)	0.001 (2)	−0.065 (3)	−0.0194 (17)
F2	0.085 (2)	0.255 (7)	0.0643 (18)	0.003 (3)	0.0218 (15)	0.049 (3)
F3	0.093 (3)	0.095 (2)	0.0627 (18)	0.0467 (16)	−0.0183 (18)	−0.0041 (12)
F1A	0.116 (6)	0.093 (4)	0.071 (3)	0.011 (4)	−0.032 (4)	−0.018 (3)
F2A	0.213 (10)	0.090 (5)	0.082 (5)	−0.027 (4)	−0.018 (5)	0.050 (3)
F3A	0.039 (3)	0.302 (15)	0.081 (5)	0.003 (6)	0.002 (3)	0.042 (8)
N1	0.0356 (6)	0.0390 (6)	0.0485 (7)	0.0048 (5)	0.0053 (5)	0.0016 (5)
N2	0.0445 (7)	0.0524 (7)	0.0604 (8)	0.0094 (6)	0.0009 (6)	0.0029 (6)
N3	0.0590 (8)	0.0662 (9)	0.0748 (10)	0.0127 (7)	0.0158 (7)	−0.0053 (7)
C1	0.0389 (7)	0.0421 (7)	0.0524 (9)	0.0057 (6)	0.0024 (7)	0.0051 (6)
C2	0.0468 (8)	0.0463 (8)	0.0498 (9)	0.0012 (6)	0.0043 (7)	0.0004 (6)
C3	0.0525 (9)	0.0530 (9)	0.0580 (10)	0.0038 (7)	0.0117 (8)	−0.0084 (7)
C4	0.0432 (8)	0.0486 (8)	0.0680 (10)	0.0103 (7)	0.0096 (8)	−0.0042 (7)
C5	0.0371 (7)	0.0400 (7)	0.0593 (9)	0.0067 (6)	0.0046 (7)	0.0022 (6)
C6	0.0451 (8)	0.0471 (8)	0.0532 (9)	0.0008 (6)	0.0045 (7)	0.0036 (6)
C7	0.0403 (7)	0.0434 (7)	0.0462 (8)	0.0040 (6)	0.0064 (6)	0.0027 (6)
C8	0.0435 (8)	0.0466 (8)	0.0509 (8)	0.0023 (6)	0.0078 (7)	0.0010 (6)
C9	0.0651 (11)	0.0746 (12)	0.0540 (10)	0.0025 (9)	−0.0037 (9)	0.0045 (8)

C10—F3A	1.249 (10)	C2—C3	1.420 (2)
C10—F2	1.273 (4)	C3—C4	1.351 (2)
C10—F1A	1.298 (7)	C3—H3A	0.9300
C10—F3	1.316 (4)	C4—C5	1.405 (2)
C10—F1	1.350 (5)	C4—H4A	0.9300
C10—F2A	1.359 (9)	C6—C7	1.379 (2)
C10—C2	1.491 (2)	C6—C9	1.486 (2)
N1—C1	1.3635 (19)	C7—C8	1.4095 (19)
N1—C7	1.3880 (18)	C9—H9A	0.9600
N1—C5	1.3931 (17)	C9—H9B	0.9600
N2—C5	1.3340 (19)	C9—H9C	0.9600
N2—C6	1.3571 (19)	C9—H9D	0.9600
N3—C8	1.1442 (17)	C9—H9E	0.9600
C1—C2	1.354 (2)	C9—H9F	0.9600
C1—H1A	0.9300
F3A—C10—F1A	115.7 (7)	C2—C3—H3A	119.8
F2—C10—F3	104.8 (4)	C3—C4—C5	119.33 (13)
F2—C10—F1	109.4 (4)	C3—C4—H4A	120.3
F3—C10—F1	102.0 (4)	C5—C4—H4A	120.3
F3A—C10—F2A	108.3 (9)	N2—C5—N1	111.00 (12)
F1A—C10—F2A	95.5 (7)	N2—C5—C4	130.66 (13)
F3A—C10—C2	115.4 (6)	N1—C5—C4	118.32 (14)
F2—C10—C2	114.5 (3)	N2—C6—C7	110.63 (14)
F1A—C10—C2	111.4 (4)	N2—C6—C9	122.40 (14)
F3—C10—C2	113.7 (3)	C7—C6—C9	126.97 (14)
F1—C10—C2	111.5 (2)	C6—C7—N1	106.29 (12)
F2A—C10—C2	108.4 (5)	C6—C7—C8	129.98 (14)
C1—N1—C7	131.48 (12)	N1—C7—C8	123.71 (13)
C1—N1—C5	122.71 (12)	N3—C8—C7	178.02 (17)
C7—N1—C5	105.77 (12)	C6—C9—H9A	109.5
C5—N2—C6	106.31 (12)	C6—C9—H9B	109.5
C2—C1—N1	118.37 (13)	C6—C9—H9C	109.5
C2—C1—H1A	120.8	C6—C9—H9D	109.5
N1—C1—H1A	120.8	C6—C9—H9E	109.5
C1—C2—C3	120.76 (15)	H9D—C9—H9E	109.5
C1—C2—C10	119.84 (14)	C6—C9—H9F	109.5
C3—C2—C10	119.40 (14)	H9D—C9—H9F	109.5
C4—C3—C2	120.49 (14)	H9E—C9—H9F	109.5
C4—C3—H3A	119.8
C7—N1—C1—C2	176.78 (13)	C6—N2—C5—N1	−0.64 (16)
C5—N1—C1—C2	−0.6 (2)	C6—N2—C5—C4	177.88 (15)
N1—C1—C2—C3	0.7 (2)	C1—N1—C5—N2	178.33 (12)
N1—C1—C2—C10	−178.43 (14)	C7—N1—C5—N2	0.40 (16)
F3A—C10—C2—C1	−22.2 (11)	C1—N1—C5—C4	−0.4 (2)
F2—C10—C2—C1	120.0 (5)	C7—N1—C5—C4	−178.32 (13)
F1A—C10—C2—C1	−156.7 (8)	C3—C4—C5—N2	−177.24 (15)
F3—C10—C2—C1	−0.4 (4)	C3—C4—C5—N1	1.2 (2)
F1—C10—C2—C1	−115.0 (5)	C5—N2—C6—C7	0.64 (17)
F2A—C10—C2—C1	99.5 (6)	C5—N2—C6—C9	−178.97 (14)
F3A—C10—C2—C3	158.6 (11)	N2—C6—C7—N1	−0.40 (16)
F2—C10—C2—C3	−59.1 (5)	C9—C6—C7—N1	179.19 (14)
F1A—C10—C2—C3	24.1 (8)	N2—C6—C7—C8	−178.74 (14)
F3—C10—C2—C3	−179.6 (3)	C9—C6—C7—C8	0.8 (3)
F1—C10—C2—C3	65.8 (5)	C1—N1—C7—C6	−177.68 (14)
F2A—C10—C2—C3	−79.7 (6)	C5—N1—C7—C6	0.00 (15)
C1—C2—C3—C4	0.1 (2)	C1—N1—C7—C8	0.8 (2)
C10—C2—C3—C4	179.24 (15)	C5—N1—C7—C8	178.48 (13)
C2—C3—C4—C5	−1.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N3i	0.93	2.45	3.384 (2)	176
C4—H4A···N2ii	0.93	2.53	3.428 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯N3i	0.93	2.45	3.384 (2)	176
C4—H4A⋯N2ii	0.93	2.53	3.428 (2)	163

Symmetry codes: (i) ; (ii) .